Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120292
Identification
Name: thiocysteine
Description:An S-substituted L-cysteine where the S-substituent is specified as sulfanyl.
Structure
Thumb
Synonyms:
  • (R)-2-amino-3-disulfanylpropanoic acid
  • 2-amino-3-disulfanylpropanoic acid
  • 2-amino-3-hydrodisulfidopropanoic acid
  • 2-amino-3-hydropersulfidopropanoic acid
  • 2-amino-3-persulfhydrylpropanoic acid
  • 3-(thiosulfeno)-alanine
  • cysteine persulfide
  • cysteine perthiol
  • S-sulfanylcysteine
  • Thiocysteine
  • thiocysteine
Chemical Formula: C3H7NO2S2
Average Molecular Weight: 153.214
Monoisotopic Molecular Weight: 153.99965
InChI Key: XBKONSCREBSMCS-REOHCLBHSA-N
InChI:InChI=1S/C3H7NO2S2/c4-2(1-8-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1
CAS number: 5652-32-4
IUPAC Name:3-disulfanyl-L-alanine
Traditional IUPAC Name: (2S)-2-amino-3-disulfanylpropanoic acid
SMILES:C(SS)C(C([O-])=O)[N+]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as cysteine and derivatives. These are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct Parent Cysteine and derivatives
Alternative Parents
Substituents
  • Cysteine or derivatives
  • Alpha-amino acid
  • D-alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Sulfenyl compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.917Not Available
Predicted Properties
PropertyValueSource
Water Solubility14.3 mg/mLALOGPS
logP-2ALOGPS
logP-2.4ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)2.04ChemAxon
pKa (Strongest Basic)8.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.99 m3·mol-1ChemAxon
Polarizability14.19 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
    Spectra
    Spectra: Not Available
    References
    References:
    • Ollagnier-de-Choudens S, Lascoux D, Loiseau L, Barras F, Forest E, Fontecave M (2003)Mechanistic studies of the SufS-SufE cysteine desulfurase: evidence for sulfur transfer from SufS to SufE. FEBS letters 555, Pubmed: 14644425
    • Mihara H, Esaki N (2002)Bacterial cysteine desulfurases: their function and mechanisms. Applied microbiology and biotechnology 60, Pubmed: 12382038
    • Kaiser JT, Bruno S, Clausen T, Huber R, Schiaretti F, Mozzarelli A, Kessler D (2003)Snapshots of the cystine lyase C-DES during catalysis. Studies in solution and in the crystalline state. The Journal of biological chemistry 278, Pubmed: 12386155
    • Kurihara T, Mihara H, Kato S, Yoshimura T, Esaki N (2003)Assembly of iron-sulfur clusters mediated by cysteine desulfurases, IscS, CsdB and CSD, from Escherichia coli. Biochimica et biophysica acta 1647, Pubmed: 12686149
    • Clausen T, Kaiser JT, Steegborn C, Huber R, Kessler D (2000)Crystal structure of the cystine C-S lyase from Synechocystis: stabilization of cysteine persulfide for FeS cluster biosynthesis. Proceedings of the National Academy of Sciences of the United States of America 97, Pubmed: 10760256
    • Kambampati R, Lauhon CT (2000)Evidence for the transfer of sulfane sulfur from IscS to ThiI during the in vitro biosynthesis of 4-thiouridine in Escherichia coli tRNA. The Journal of biological chemistry 275, Pubmed: 10753862
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    METABOLIGHTSMTBLC28839
    HMDBHMDB03585
    CHEBI9551
    PUBCHEM25203540
    LIGAND-CPDC01962
    CAS5652-32-4